What No One Tells You About Pursuing Your Dream Career

Everyone talks about getting the dream career, but no one really talks about the discomfort along the way or what happens when you start reaching it. 

We are taught at a young age to choose a dream career and work towards that our whole lives with all the applause and motivational quotes along the way. And of course, achieving your dream career is tough. It comes with years of education, grind, studying,  uncertainty etc. But what happens when you have to actually start achieving it? 

When you start going 5, 10, 15 years into your career, you start to really work towards a career direction. And as you work towards your career, that safe and steady applause of school and achievement checkboxes fades away. 

Today I want to talk about the uncomfortable, non-instagrammable parts of achieving your dream career. What happens when you start achieving milestones and feel out of place? How do you keep going after you achieve the first step of your dream career and what happens if something unexpected comes along the way?

Let’s get started!


1. Peaks and Valleys of Impostor Syndrome

Impostor syndrome is a mindset in which we doubt our skills, talents or accomplishments. It’s fueled by the fear of being exposed as a “fraud” and it can be really easy to feel when we reach an accomplishment, and the feeling didn’t live up to the vision. 

This is especially prominent when we graduate from school or receive some kind of job title. You might have a vision of what it feels like to finally say you are a “Director,” or a “Consultant” or a “Lawyer” but really, as a person, you are not that different from the person you were last week when you didn’t receive that title yet. 

Impostor syndrome can hit at any minute and it can hit hard. 

Honestly, impostor syndrome never really goes away, because it is a type of fear – a fear of being found out as a fraud, that you really don’t know as much as you don’t think you do, and that you really don’t belong. 

And while it can be easy to feel like this is something you just repress, deny, or avoid – it’s easy to understand how impostor syndrome works. 

Impostor syndrome is also known as the Dunning-Kruger effect in psychology. It’s when you gain more knowledge that you feel less confident because you then know how much knowledge you don’t have. 

When you first start off in your career, it can be easy to have this idealistic outlook on your career. But as you get into it, you learn all about the things you didn’t even know existed. 

And it can be incredibly overwhelming. That’s when the self-doubt kicks in. 

But the great thing about this effect is that if you continue to learn and grow, the more your confidence will grow. In the Dunning Kruger effect, the initial high and optimism are called the peak of stupidity and the dip is called the valley of despair and as you move through your career, your knowledge and confidence will increase steadily through a slope of enlightenment. 

That’s why so many new graduates walk around with a lot of optimism and overconfidence and people with lots of years of experience start to feel self-doubt because once you’ve been in your industry for a while, you know how much there is to still learn. 

And this effect repeats itself because every time you try something new, it will continue. BUT, the great thing about working about your impostor syndrome is that once you understand it and get the hang of it, it gets easier to move through. The initial dip is not as steep, and you move through the slope of enlightenment easier. 


2. Rejection 

One of the things I really dislike about the career space is the toxic positivity it can encompass and encourage. Going for your dream career isn’t just about getting job offers and making lots of money all the time, it comes with rejection and even the successes can feel super uncomfortable. 

Because to get to your dream career, you have to face a lot of rejection. Everyone faces rejection, but that’s not the fun, shiny part we share with anyone. 

And one of the greatest things anyone can learn to do is separate the rejection of your career from yourself. I’ve been rejected so many times in my career, and I’ve learned that the most important skill, more than any resume hack or magical interview answer, is learning how to come back from rejection and separate it from you as a person and your career journey. 

Feeling rejection is not a reflection of yourself at all. It might not have been the right fit, the company might have liked you, but they perceived someone else as a better fit, not a better human being or person on a whole.

And this whole process is incredibly uncomfortable. 

When you start achieving your dream career, you are also going to start facing more rejection, as you should. Because that means you are going for something scary, something extremely difficult. If it was easy, then it’s actually a lateral career move and you are keeping yourself safe. 

As you move through your career, rejection is a good thing because it means you are going really working to make big strides in your career and you can take them as learning lessons.


3. Uncomfortable Growth & The Upper Limit Problem

Now once you reach a certain level in your career, you will start to get restless. You are no longer new to your job or industry, but you might be struggling to take the next step forward. 

You have the skills, you have the experience, but you are hitting a ceiling. 

This is the part of career planning that is uncomfortable. One thing I really remind myself is that “what got you here, won’t get you there,” and that really applies to career growth. 

The same things that might have gotten you to this level of your career – working overtime, relying on school accomplishments, relying on high school resume/interview tips, don’t get you to the next level. 

Midway through your career you will start to feel stuck and push yourself to do things like negotiating your value, advocate for work-life balance (because your mental health can’t take the burnout hustle culture anymore, and really push new ideas, and take leadership instead of listening to others. 

And this feeling is very uncomfortable. You can get hit with that impostor syndrome again, and there is also a term for this type of growth stagnation as well, it’s called the upper limit problem.

The upper limit problem is when you start to feel scared to take yourself to the next level because of fear of failure and a desire to want to stay comfortable. This can manifest in many different ways like worrying about scenarios that you’ve imagined could happen, being scared to out succeed your friends, family, or partner, or even self-sabotage like purposely looking for excuses not to work towards your goals or even feeling sick is a form of self-sabotage as well. 

The upper limit problem is when you feel so paralyzed by the fear of failure and discomfort that you find ways to not have to go through with it. 

This is a very normal feeling and it’s important again to understand this is a phase in achieving your dream career and if you address it properly, it is something can learn to manage with your career instead of having to be paralyzed by. 

Achieving your dream career is uncomfortable and that’s okay.


4. Forgetting It Will Never Get Better Than This

One of the things I tell myself every day is that it will never get better than this because, at one point in my life, this is what I wanted. 

I remember all the years I worked so hard to graduate from school and land my dream job.

And if you race on to the next thing, then I promise you, you will never be satisfied. No one can do it all in their career. There isn’t enough time, resources, or capability to do everything. 

We all choose career paths, and that’s what it is, a career path. And other people take different paths which is what makes life exciting and unique. 

So at every point of your career, it’s really important to celebrate your achievements and it’s also okay to say “this is my dream job” even if you have more career goals along the way. I firmly believe a dream job is a mindset. It’s something we construct within ourselves because my dream job will greatly differ from someone else’s. 

While it is easy to always chase “the next best thing,” it’s so important to reward yourself for how far you come.


Lastly, if you are looking to overcome impostor syndrome, rejection, upper limit problem, and so much more to really advance your career, I invite you to book a FREE 1:1 Career Coaching Discovery Call here. Unsure of where to start? We’ll figure that out!

For years I let these things pull me back subconsciously and now I am able to take decisive action and have the confidence to figure it out along the way. I know it’s truly easier said than done, but this week I invite you to take a small step in reflecting on how to advance in your career.

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